Preparation and characterization of adefovir dipivoxil–stearic acid cocrystal with enhanced physicochemical properties

Seo, Jeong-Woong; Hwang, Kyu-Min; Lee, Sung-Hoon; Kim, Dong-Wook; Park, Eun-Seok

doi:10.1080/10837450.2017.1334664

Cited by 21 publications

(15 citation statements)

References 46 publications

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“…Interestingly, the permeability was also improved for RIV-IA cocrystals with low solubility, thus indicating that the solubility was not always positively related to permeability. The results were similar to previous report from Seo et al ( Seo et al, 2018 ), who found that cocrystals had no remarkable impact on the apical-to-basal transport rate of drug although the in vitro dissolution was enhanced. In addition, the physical mixtures had different behavior from cocrystals, which might be attributed to the formation of molecular aggregates in solution ( Emami et al, 2018 ).…”

Section: Resultssupporting

confidence: 92%

Preparation, characterization, and pharmacokinetics of rivaroxaban cocrystals with enhanced in vitro and in vivo properties in beagle dogs

Meng¹,

Tan²,

Yao³

et al. 2022

International Journal of Pharmaceutics: X

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Section: Resultssupporting

confidence: 92%

Preparation, characterization, and pharmacokinetics of rivaroxaban cocrystals with enhanced in vitro and in vivo properties in beagle dogs

Meng¹,

Tan²,

Yao³

et al. 2022

International Journal of Pharmaceutics: X

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“…Prior art permeability/diffusion data on multicomponent solids of BCS class I–IV drugs indicates that improved properties are correlated with higher log P of the coformer, drug-coformer interactions/weaker heterosynthons, layer crystal structures, lower melting point/crystal density/lattice energy, enhanced solubility/dissolution rate/molecular mobility, and polar/nonpolar interactions of the binary solid. − ,− Table S3 summarizes a total of 19 research articles based on the multicomponent solids (with 3D coordinates) of a drug with modulation of diffusion behavior reported in the literature. The presence of a hydrophobic moiety like an aromatic ring (BA/DHBA) or cyclic amide (CPR) in the ECB multicomponent solids diffused the drug much better compared to the hydrophilic coformers (MLN/MLE) through the dialysis membrane.…”

Section: Results and Discussionmentioning

confidence: 99%

Tuning Diffusion Permeability of an Anti-Retroviral Drug, Emtricitabine, via Multicomponent Crystallizations

Palanisamy

Sanphui

Jyothi

et al. 2021

Crystal Growth & Design

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Emtricitabine (ECB) is an anti-retroviral drug that inhibits HIV reverse transcriptase and prevents transcription of RNA to DNA. ECB exhibits high solubility and low permeability (log P < 0). To modify the diffusion behavior of ECB, a high throughput cocrystal screening has been carried out with coformers that contain carboxylic acid/amide functionalities via solvent assisted grinding. The screening study resulted in the formation of cocrystals with benzoic acid (BA), caprolactam (CPR), and salts with 2,6-dihydroxybenzoic acid (DHBA), malonic acid (MLN), maleic acid (MLE), and saccharin (SAC), which were confirmed with single crystal X-ray diffraction. In addition, 15N solid state NMR spectroscopy was exploited to define the ionization state of the multicomponent systems. The 2-aminopyrimidine homodimer of the cytosine analogue in the ECB is replaced by aminopyrimidine···carboxylic acid/amide in the cocrystals and aminopyrimidinium···carboxylate/saccharinate heterosynthons in the salts. The terminal hydroxyl group of the ECB forms a hydrogen bond with its carbonyl group, which is consistent in the ECB–BA cocrystal, ECB–DHBA and ECB–MLN salts. In addition, the hydroxyl group of ECB is hydrogen bonded with the relatively stronger acceptors like the carbonyl/sulfonyl group of caprolactam, maleate, and saccharinate in their corresponding multicomponent crystals. The diffusion studies of ECB multicomponent crystals using a Franz diffusion cell suggest that the ECB–BA cocrystal exhibited an enhanced diffusion and flux compared to that of native drug and other multicomponent crystals. An inverse correlation was observed partially between the flux values with crystal densities and binding energies of the ECB multicomponent systems.

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“…The batch mode cocrystallization techniques include mechanochemical methods such as Solid-State grinding [ 151 , 152 ], Liquid-Assisted grinding [ 151 ], Ion and Liquid-Assisted Grinding [ 153 ] and solvent-based techniques such as slow evaporation [ 154 ], ultrasound-assisted cocrystallization [ 155 , 156 ], slurry conversion [ 140 , 157 ] or solvent-mediated phase transformation [ 158 ], generation of cocrystals from moisture [ 159 , 160 ] and anti-solvent precipitation (Liquid Anti-Solvent precipitation) [ 161 ] and Gas Anti-Solvent precipitation [ 162 ]. Table 7 presents the principle involved behind these batch cocrystallization techniques [ 151 , 153 , 154 , 155 , 159 , 161 , 162 , 163 ]. Mechanochemical methods, ultrasound-assisted cocrystallization, cocrystal generation using moisture are discussed in the Section 5.1 in detail.…”

Section: Synthesis Of Cocrystalsmentioning

confidence: 99%

Engineering Cocrystals of Poorly Water-Soluble Drugs to Enhance Dissolution in Aqueous Medium

2018

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Biopharmaceutics Classification System (BCS) Class II and IV drugs suffer from poor aqueous solubility and hence low bioavailability. Most of these drugs are hydrophobic and cannot be developed into a pharmaceutical formulation due to their poor aqueous solubility. One of the ways to enhance the aqueous solubility of poorlywater-soluble drugs is to use the principles of crystal engineering to formulate cocrystals of these molecules with water-soluble molecules (which are generally called coformers). Many researchers have shown that the cocrystals significantly enhance the aqueous solubility of poorly water-soluble drugs. In this review, we present a consolidated account of reports available in the literature related to the cocrystallization of poorly water-soluble drugs. The current practice to formulate new drug cocrystals with enhanced solubility involves a lot of empiricism. Therefore, in this work, attempts have been made to understand a general framework involved in successful (and unsuccessful) cocrystallization events which can yield different solid forms such as cocrystals, cocrystal polymorphs, cocrystal hydrates/solvates, salts, coamorphous solids, eutectics and solid solutions. The rationale behind screening suitable coformers for cocrystallization has been explained based on the rules of five i.e., hydrogen bonding, halogen bonding (and in general non-covalent bonding), length of carbon chain, molecular recognition points and coformer aqueous solubility. Different techniques to screen coformers for effective cocrystallization and methods to synthesize cocrystals have been discussed. Recent advances in technologies for continuous and solvent-free production of cocrystals have also been discussed. Furthermore, mechanisms involved in solubilization of these solid forms and the parameters influencing dissolution and stability of specific solid forms have been discussed. Overall, this review provides a consolidated account of the rationale for design of cocrystals, past efforts, recent developments and future perspectives for cocrystallization research which will be extremely useful for researchers working in pharmaceutical formulation development.

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Preparation and characterization of adefovir dipivoxil–stearic acid cocrystal with enhanced physicochemical properties

Cited by 21 publications

References 46 publications

Preparation, characterization, and pharmacokinetics of rivaroxaban cocrystals with enhanced in vitro and in vivo properties in beagle dogs

Preparation, characterization, and pharmacokinetics of rivaroxaban cocrystals with enhanced in vitro and in vivo properties in beagle dogs

Tuning Diffusion Permeability of an Anti-Retroviral Drug, Emtricitabine, via Multicomponent Crystallizations

Engineering Cocrystals of Poorly Water-Soluble Drugs to Enhance Dissolution in Aqueous Medium

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